It connoted something like 'I'm a little cooler than you.

People are finally catching on. It's a chic look that's really practical. It allows for different temperatures. You can take the hat off, take the scarf off. On warm days you can just turn your collar up.

It's one of those masculine paradigms - the pirate - like the cowboy and the all-American prep, that crops up from time to time in men's fashion. They do get kind of recycled.